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Compare 20 Condo Rentals in Historic Route 66 with updated reviews, rates, and availability.

Visitors Love the Location, I Love the View!
Miscellaneous

Visitors Love the Location, I Love the View!

10.0 out of 10, Exceptional, (390)
"Great place! The view is beautiful especially if you catch the sunrise. Everything we needed to make our Thanksgiving dinner was in the kitchen. The place was comfortable, welcoming and well stocked. The owner was very responsive and had great suggestions about things to do in the area."
Visitors Love the Location, I Love the View!
NEW LUXURY CONDO WITH PATIO DECK
Fridge, microwave, oven, stovetop

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (152)
"We had a great stay, location was great, very clean, beautifully remodeled, the bathroom felt like a 5 star hotel with all the upgrades they've done. The first night the refrigerator stopped working, they immediately went over to try to fix it but were unsuccessful, they offered to purchase ice for us and by the next day they had purchased and installed a new refrigerator. Overall, we had a great experience and would definitely stay here again. "
NEW LUXURY CONDO WITH PATIO DECK
Stunning 3 BR in prime Chicago location
Fridge, microwave, oven, stovetop

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (83)
"Very close to the train. Good location "
Stunning 3 BR in prime Chicago location
Hidden East Village Gem
Terrace/patio

Hidden East Village Gem

9.6 out of 10, Exceptional, (29)
"Perfect spot for a family. Visiting for husband’s conference. Great neighborhood and easy to get to all tourist attractions. Highly recommend. All our needs were anticipated. "
Hidden East Village Gem
Left Frame Lofts 210, Where history meets Luxury
Interior

Left Frame Lofts 210, Where history meets Luxury

9.8 out of 10, Exceptional, (20)
"The lifts are always clean and the esthetic of each loft is astonishing this is my 2nd time booking and I will continue to do so ! The host is great and responsive !"
The price is ￥25,232
￥51,525 total
includes taxes & fees
Dec 22 - Dec 23
Left Frame Lofts 210, Where history meets Luxury
Walking distance to restaurants, shops and Lake Michigan,
Exterior

Walking distance to restaurants, shops and Lake Michigan,

9.8 out of 10, Exceptional, (194)
"The apartment is beautifully decorated and updated. Ross, the host gave us a welcome tour and everything was clearly explained. Beds are comfortable and rooms are spacious. We were relieved our rental minivan (just barely) fit in the garage! We did the kitchen wasn't as well equipped as we would have liked, but we were cooking a Thanksgiving meal which may have been a bit ambitious. The meal turned out well and we enjoyed our stay immensely!"
Walking distance to restaurants, shops and Lake Michigan,
3 #3A - 3 Bedroom Condo w Parking - Chinatown, McCormick Place, Wintrust Arena
Fridge, microwave, coffee/tea maker, dining tables

3 #3A - 3 Bedroom Condo w Parking - Chinatown, McCormick Place, Wintrust Arena

9.8 out of 10, Exceptional, (21)
"This was the perfect spot for our family's getaway. We love going to chinatown and it was ready to get to chinatown with walking distance. Definitely recommend!"
3 #3A - 3 Bedroom Condo w Parking - Chinatown, McCormick Place, Wintrust Arena
Perfect Weekend Getaway! Condo With Great River Views! Pool!
Outdoor dining

Perfect Weekend Getaway! Condo With Great River Views! Pool!

9.8 out of 10, Exceptional, (129)
"The unit was perfect for a weekend getaway! "
The price is ￥18,428
￥23,460 total
includes taxes & fees
Dec 20 - Dec 21
Perfect Weekend Getaway! Condo With Great River Views! Pool!
Experience charm in Historic Eastside, just a quick 5min drive to Santa Fe Plaza
Pool

Experience charm in Historic Eastside, just a quick 5min drive to Santa Fe Plaza

9.4 out of 10, Exceptional, (41)
"I love the koi pond, the entry was leveled a bit higher but we rented a small suv that was perfect, the bed was amazingly comfortable to sleep on. Everything was clean, close to everything. I would recommend this casita. "
Experience charm in Historic Eastside, just a quick 5min drive to Santa Fe Plaza
Experience Chicago living near United Center
Fridge, microwave, oven, stovetop

Experience Chicago living near United Center

9.4 out of 10, Exceptional, (12)
"Our family stayed for a corporate training and we had a great experience. The neighborhood wasn't the best but we felt very secure with having a garage to use. Very thankful for the quick communication! from the p "
Experience Chicago living near United Center
Placid home with new fireplace, full kitchen, gas grill, patio, & washer/dryer
Fridge, microwave, oven, stovetop

Placid home with new fireplace, full kitchen, gas grill, patio, & washer/dryer

9.4 out of 10, Exceptional, (18)
"It was nice to relax after a long day of moving kids into college."
Placid home with new fireplace, full kitchen, gas grill, patio, & washer/dryer
Brilliant Downtown Chicago 3-Bedroom Condominium
3 bedrooms, desk, iron/ironing board, travel crib

Brilliant Downtown Chicago 3-Bedroom Condominium

10.0 out of 10, Exceptional, (43)
"Apartment was as shown on Vrbo website - comfortable and clean. Good location, easy access and nearby parking. Kitchen well equipped, bathrooms modern and good towels and bed linens. Only modest issue is that the heating system is really quite loud when on. "
Brilliant Downtown Chicago 3-Bedroom Condominium
Walking distance to restaurants, shops and Lake Michigan,
Exterior

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (174)
"We were very pleased with the property. Stayed there over the Thanksgiving holiday & weekend while visiting my older daughter. Nice neighborhood & easy location to get to other parts of the city. Everything was as depicted in the description and communication with management was excellent. Would stay here again."
Walking distance to restaurants, shops and Lake Michigan,
Unique to Santa Fe, this industrial condo is 5 mins to Railyard, 7 mins to Plaza
Fridge, microwave, oven, stovetop

Unique to Santa Fe, this industrial condo is 5 mins to Railyard, 7 mins to Plaza

10.0 out of 10, Exceptional, (11)
"Quirky, charming and the perfect space for me and my two best friends!"
Unique to Santa Fe, this industrial condo is 5 mins to Railyard, 7 mins to Plaza
Cozy Southwest Style Santa Fe Condo!
Fridge, microwave, stovetop, dishwasher

Cozy Southwest Style Santa Fe Condo!

10.0 out of 10, Exceptional, (46)
"Very quiet and peaceful. Beautiful spot close to downtown Santa Fe. Very clean facility. "
Cozy Southwest Style Santa Fe Condo!
The Upscale Getaway Near Downtown
Fridge, microwave, oven, stovetop

The Upscale Getaway Near Downtown

9.8 out of 10, Exceptional, (81)
"Alex was helpful in every way possible and the place was perfect in every way and so well appointed "
The Upscale Getaway Near Downtown
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
Fridge, microwave, oven, stovetop

MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking

9.4 out of 10, Exceptional, (22)
"We could not have asked for a better host & the place was awesome. Thank you"
The price is ￥41,614
￥83,431 total
includes taxes & fees
Jan 6 - Jan 7, 2025
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
Bear Paw
Condo | Private kitchen | Full-size fridge, microwave, oven, stovetop

Bear Paw

3.5 star property
7.6 out of 10, Good, (5)
"Best feature of the property is a very nice view from the balcony. However, 3 levels including a loft (surprise), also 1 and1/2 baths, (not 2). Patio furniture and many other items should be updated. Window in loft will not close, (nights are getting cold). A really good deep cleaning is overdue and would be a nice touch for the arriving guests. We were also asked to take out the trash and begin the laundry before departure. What was the cleaning fee for??"
Bear Paw
Your Riverfront Relaxing Vacation Home
Exterior

Your Riverfront Relaxing Vacation Home

9.8 out of 10, Exceptional, (55)
"The condo was in a great shape and Laura was a great host and made everything run smoothly!"
Your Riverfront Relaxing Vacation Home
Parking included and longer stays encouraged in Lincoln Park
Point of interest

Parking included and longer stays encouraged in Lincoln Park

9.8 out of 10, Exceptional, (62)
"The apartment was as promised, home like with basic pantry supplies. Close to downtown and walkable to Second City."
Parking included and longer stays encouraged in Lincoln Park
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Historic Route 66

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (623)
"We stayed at the Sentral with friends to take in the holiday sights around Chicago. The room was spacious and clean, though a little worn in areas. Having a kitchen, plus a washer & dryer was great. And the city views were incredible. The amenities (pool, gym, game room) on the 7th floor were phenomenal! We found cheaper parking in a nearby garage, but the valet option is nice. And having restaurants and a grocery nearby was super convenient."
The price is ￥17,829
￥25,437 total
includes taxes & fees
Jan 15 - Jan 16, 2025
Sentral Michigan Avenue
Junipine Resort
Terrace/patio

Junipine Resort

3.5 star property
9.2 out of 10, Wonderful, (1937)
"Was promised a bottle of wine per stay did not receive, place was beautiful and quite, hot water in shower was not working properly, stays hot for 3 mins and Luke warm afterwards not getting hot at all, the light in the shower was glitchy sometimes it worked and sometimes not more on the sometime not. Not mad at all just pointing out minor fixes needed. Junipine was so amazing that we will be back again. Destination was beautiful so beautiful "
The price is ￥44,708
￥50,923 total
includes taxes & fees
Dec 20 - Dec 21
Junipine Resort
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (342)
"Good location. Full kitchen and clothes washer/dryer in suite were awesome amenities! Blinds were missing a few blades which was annoying. Tub could use a reglaze parking is close by but having a deal with the lot would be nice"
Kasa Magnificent Mile Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.